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It finds its application as a pharmaceutical intermediate and in the synthesis of aspidospermidine alkaloids.
Crosby U. Rogers and B. B. Corson. One-Step Synthesis of 1,2,3,4-Tetrahydrocarbazole and 1,2-Benzo-3,4-dihydrocarbazole.J. Am. Chem. Soc.,1947,69(11), 2910-2911.
Anahí Urrutia, et. al. Synthesis of aspidospermidine alkaloids from 1,2,3,4-tetrahydrocarbazole: Total stereoselective synthesis of (±)-18-noraspidospermidine.Tetrahedron.,2014,55(36), 11095-11108.
Deprotonation with excess superbasic n-BuLi/KO-t-Bu to give the N,ɑ-dianion has been studied in a variety of ether solvents. Formation of substantial amounts of the ɑ-ethyl derivative was observed with Et2O and THF, and also, remarkably, with various alkyl methyl ethers; e.g. in n-BuOMe, the ɑ-ethyl product was obtained in 60% yield. The ethyl group originates from the interaction of the solvent with the strong base, confirmed by the detection of ethylene in the absence of the tetrahydrocarbazole substrate: J. Org. Chem., 60, 8334 (1995). ɑ-Ethylation also occurred with 2-ethylindole, but not with 2-methyl- or 2-isopropyl analogues.
Photooxygenation with singlet oxygen, followed by reduction of the expected hydroperoxide to the allylic alcohol, is accompanied by ring contraction to a spiro ketone. The same product is formed in high yield on treatment of the spiroketone with mineral acid: J. Org. Chem., 61, 810 (1996):
Mentions de danger (UE): H303-H315-H319-H335
May be harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Mentions de prudence: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.